Carbonyl fluoride, reactions

Carbonyl fluoride, COF2, and oxygen difluoride react in the presence of cesium fluoride catalyst to give bis(trifluorylmethyl)trioxide [1718-18-9] CF OOOCF (31). CF OOF has been isolated from the reaction in the presence of excess OF2 (32). 

Tetrafluoroethylene undergoes addition reactions typical of an olefin. It bums in air to form carbon tetrafluoride, carbonyl fluoride, and carbon dioxide (24). Under controlled conditions, oxygenation produces an epoxide (25) or an explosive polymeric peroxide (24). Trifluorovinyl ethers,... 

Carbonyl fluoride, COF2, is an important intermediate for organic fluorine compounds. It can be prepared by the following reaction ... 

Reaction to give tetrafluorooxathietane 2,2-dioxide (tetrafluoroethane sultone) had been used industrially and uneventfully, but reaction with excess sulfur trioxide may cause explosive decomposition to carbonyl fluoride and sulfur dioxide [1]. An incident involving the same explosion hazard was reported 11 years later [2], Use of inert gas to prevent explosion has been patented [3],... 

The enantioselective addition of a nucleophile to a carbonyl group is one of the most versatile methods for C C bond formation, and this reaction is discussed in Chapter 2. Trifluoromethylation of aldehyde or achiral ketone via addition of fluorinated reagents is another means of access to fluorinated compounds. Trifluoromethyl trimethylsilane [(CF SiCFs] has been used by Pra-kash et al.87 as an efficient reagent for the trifluoromethylation of carbonyl compounds. Reaction of aldehydes or ketones with trifluoromethyltrime-thylsilane can be facilitated by tetrabutyl ammonium fluoride (TBAF). In 1994, Iseki et al.88 found that chiral quaternary ammonium fluoride 117a or 117b facilitated the above reaction in an asymmetric manner (Scheme 8-42). 

Carbonyl fluoride is prepared by the reaction of carbon monoxide with fluorine gas or silver fluoride ... 

Elemental composition C 18.19%, F 57.57%, O 24.24%. Carbonyl fluoride may be analyzed by FTIR, GC or GC/MS. For the GC analysis, it may be transported with the carrier gas helium from the reaction vessel into a cryo-genically cooled injector port, then thermally desorbed and analysed by FID. The system should be free of moisture. The characteristic ions for mass spectroscopic identification are 66, 26, and 40. 

Oxygen dilluoride reacts with carbonyl fluoride, COF2, in the presence of a catalyst, cesium fluoride, to form bis(trifluorylmethyl)trioxide, CF3OOOCF3 (Solomon, Irvine J. 1980. Kirk-Othmer Encyclopedia of Chemical Technology, ed., Vol. 3, pp 773-75. New York John Wiley Sons). The overall reaction is as follows ... 

Hypochlorites are obtained by reaction of fluorinated carbonyl compounds, such as carbonyl fluoride, with an alkali metal fluoride and chlorine fluoride [62, 120]... 

In any of the fluorinated alkoxides made this way there must always be a fluorine attached to the a-carbon. There is in fact an equilibrium between the metal perfluoroalkoxide and the metal fluoride and carbonyl fluoride compound. Thus these Group IA metal alkoxides cannot be used in metathe-tic reactions to prepare other metal alkoxides. For example, R3SiCl and NaOCF(CF3)2 react to yield RjSiF, NaCl and (CF3)2CO rather than R3SiOCF(CF3)2.138... 

Carbonyl fluoride can be prepared by any of several methods, including the conversion of carbonyl chloride to the fluoride by such reagents as hydrogen fluoride1 and antimony (III) fluoride.2 The direct combination of carbon monoxide and fluorine is another route to this fluoride, but carbon tetrafluoride is a by-product of the reaction.8 A particularly suitable laboratory preparation of carbonyl fluoride is the fluorination of carbon monoxide by silver (II) fluoride.4 This method, described below, gives directly carbonyl fluoride of rather high purity without recourse to a low-temperature distillation. 

A schematic diagram of the apparatus used for preparing carbonyl fluoride from carbon monoxide and silver(II) fluoride is shown in Fig. 17. Cylinders of helium and carbon monoxide are connected through flowmeters and a pressure-release device to the copper reaction tube (47 in. long, 1-J in. diameter). A smaller copper vessel containing sodium fluoride pellets is connected with copper tubing and rubber fit-... 

Yields of carbonyl fluoride obtained by this method range from 70 to 85%. The major contaminant in the frozen product is carbon dioxide. This substance may be present as an impurity in the carbon monoxide or may result from hydrolysis of carbonyl fluoride by traces of moisture in the apparatus. Carbonyl fluoride better than 99% pure is obtained if commercial carbon monoxide is purified before the reaction. ... 

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